2-(7-Amino-1,2,4,5-tetrahydro-3h-3-benzazepin-3-yl)-n,n-dimethylacetamide → 2-[5-Chloro-2-(3-dimethylcarbamoylmethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamino)-pyrimidin-4-ylamino]-N-ethyl-3-fluoro-benzamide
Reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([CH2:11][C:12]([N:14]([CH3:16])[CH3:15])=[O:13])[CH2:9][CH2:10][C:4]=2[CH:3]=1.Cl[C:20]1[N:25]=[C:24]([NH:26][C:27]2[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:28]=2[C:29]([NH:31][CH2:32][CH3:33])=[O:30])[C:23]([Cl:39])=[CH:22][N:21]=1>>[Cl:39][C:23]1[C:24]([NH:26][C:27]2[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:28]=2[C:29]([NH:31][CH2:32][CH3:33])=[O:30])=[N:25][C:20]([NH:1][C:2]2[CH:18]=[CH:17][C:5]3[CH2:6][CH2:7][N:8]([CH2:11][C:12](=[O:13])[N:14]([CH3:15])[CH3:16])[CH2:9][CH2:10][C:4]=3[CH:3]=2)=[N:21][CH:22]=1Participants
3
Reactant 2
Product 1
Procedure
2-[5-Chloro-2-(3-dimethylcarbamoylmethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamino)-pyrimidin-4-ylamino]-N-ethyl-3-fluoro-benzamide was prepared from 2-(7-amino-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N,N-dimethyl-acetamide and 2-(2,5-dichloro-pyrimidin-4-ylamino)-N-ethyl-3-fluoro-benzamide in an analogous manner to Example 308c. Product isolated as a yellow foam (137 mg, 47%). LCMS (m/e) 540 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.57 (s, 1H), 8.08 (s, 1H), 7.38-7.25 (m, 3H), 7.15 (s, 1H), 7.10 (d, 1H, J=7.8 Hz), 6.90 (d, 1H, J=7.8 Hz), 6.82 (s, 1H), 6.14-6.07 (m, 1H), 3.44-3.35 (m, 2H), 3.28 (s, 2H), 3.15 (s, 3H), 3.00 (s, 3H), 2.89-2.83 (m, 2H), 2.80-2.73 (m, 2H), 2.70-2.61 (m, 4H), 1.14 (t, 3H, J=7.3 Hz).
Sources & evidence
- ORD record
- ord-544c92f4eba945f2a22a287fe0b0080b
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08148391B2
Reaction notes
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